CA2969239C - Method for preparing sodium free ethyleneamine polyphosphate (eappa) for flame retardant uses - Google Patents

Method for preparing sodium free ethyleneamine polyphosphate (eappa) for flame retardant uses Download PDF

Info

Publication number: CA2969239C
Authority: CA; Canada
Prior art keywords: eappa; ppa; reaction; molecular weight; temperature
Prior art date: 2014-12-12
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Active

Application number

CA2969239A

Other languages

English (en)

French (fr)

Other versions

CA2969239A1 (en

Inventor

Robert Valentine Kasowski

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Individual

Original Assignee

Individual

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2014-12-12

Filing date

2015-12-12

Publication date

2022-04-26

2015-12-12 Application filed by Individual filed Critical Individual

2016-06-16 Publication of CA2969239A1 publication Critical patent/CA2969239A1/en

2022-04-26 Application granted granted Critical

2022-04-26 Publication of CA2969239C publication Critical patent/CA2969239C/en

Status Active legal-status Critical Current

2035-12-12 Anticipated expiration legal-status Critical

Links

UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 title claims abstract description 108
229920000388 Polyphosphate Polymers 0.000 title claims abstract description 41
239000001205 polyphosphate Substances 0.000 title claims abstract description 41
235000011176 polyphosphates Nutrition 0.000 title claims abstract description 41
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 title claims abstract description 33
239000011734 sodium Substances 0.000 title claims abstract description 33
229910052708 sodium Inorganic materials 0.000 title claims abstract description 33
238000000034 method Methods 0.000 title claims description 71
239000003063 flame retardant Substances 0.000 title abstract description 57
RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 title abstract description 48
229920000137 polyphosphoric acid Polymers 0.000 claims abstract description 200
238000006243 chemical reaction Methods 0.000 claims abstract description 101
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 97
239000007864 aqueous solution Substances 0.000 claims abstract description 15
239000002904 solvent Substances 0.000 claims abstract description 9
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 62
238000002156 mixing Methods 0.000 claims description 30
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 26
238000010438 heat treatment Methods 0.000 claims description 16
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 15
VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 14
230000004580 weight loss Effects 0.000 claims description 12
FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims description 8
LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 claims description 5
238000006482 condensation reaction Methods 0.000 claims 3
238000002411 thermogravimetry Methods 0.000 claims 2
239000012299 nitrogen atmosphere Substances 0.000 claims 1
229920000642 polymer Polymers 0.000 abstract description 43
150000001875 compounds Chemical class 0.000 abstract description 24
239000000203 mixture Substances 0.000 description 82
239000000047 product Substances 0.000 description 65
239000006188 syrup Substances 0.000 description 65
235000020357 syrup Nutrition 0.000 description 64
238000005342 ion exchange Methods 0.000 description 45
239000000243 solution Substances 0.000 description 44
238000009833 condensation Methods 0.000 description 42
230000005494 condensation Effects 0.000 description 42
239000000446 fuel Substances 0.000 description 40
230000015572 biosynthetic process Effects 0.000 description 30
239000004593 Epoxy Substances 0.000 description 26
239000000523 sample Substances 0.000 description 26
238000002474 experimental method Methods 0.000 description 23
230000004907 flux Effects 0.000 description 20
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 18
239000000314 lubricant Substances 0.000 description 17
239000011248 coating agent Substances 0.000 description 16
238000000576 coating method Methods 0.000 description 16
230000008569 process Effects 0.000 description 16
238000011068 loading method Methods 0.000 description 14
235000011007 phosphoric acid Nutrition 0.000 description 13
230000004888 barrier function Effects 0.000 description 12
239000007788 liquid Substances 0.000 description 12
230000002829 reductive effect Effects 0.000 description 12
239000007787 solid Substances 0.000 description 12
238000009835 boiling Methods 0.000 description 11
238000011109 contamination Methods 0.000 description 11
239000004615 ingredient Substances 0.000 description 11
229910052751 metal Inorganic materials 0.000 description 11
239000002184 metal Substances 0.000 description 11
229920001778 nylon Polymers 0.000 description 11
229920002302 Nylon 6,6 Polymers 0.000 description 10
239000004743 Polypropylene Substances 0.000 description 10
238000001125 extrusion Methods 0.000 description 10
239000002253 acid Substances 0.000 description 9
230000007797 corrosion Effects 0.000 description 9
238000005260 corrosion Methods 0.000 description 9
239000000155 melt Substances 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
239000004677 Nylon Substances 0.000 description 8
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
239000002585 base Substances 0.000 description 7
230000018044 dehydration Effects 0.000 description 7
238000006297 dehydration reaction Methods 0.000 description 7
239000000835 fiber Substances 0.000 description 7
239000002699 waste material Substances 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 6
XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 6
238000001035 drying Methods 0.000 description 6
239000010408 film Substances 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
229920013639 polyalphaolefin Polymers 0.000 description 6
-1 polypropylene Polymers 0.000 description 6
235000019830 sodium polyphosphate Nutrition 0.000 description 6
239000007921 spray Substances 0.000 description 6
239000000126 substance Substances 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
125000003700 epoxy group Chemical group 0.000 description 5
229910021485 fumed silica Inorganic materials 0.000 description 5
239000007789 gas Substances 0.000 description 5
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 5
239000003973 paint Substances 0.000 description 5
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 5
229920000647 polyepoxide Polymers 0.000 description 5
230000009467 reduction Effects 0.000 description 5
238000007086 side reaction Methods 0.000 description 5
238000012360 testing method Methods 0.000 description 5
229920001169 thermoplastic Polymers 0.000 description 5
229920001187 thermosetting polymer Polymers 0.000 description 5
229920000742 Cotton Polymers 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
239000004433 Thermoplastic polyurethane Substances 0.000 description 4
238000013459 approach Methods 0.000 description 4
230000008901 benefit Effects 0.000 description 4
230000015556 catabolic process Effects 0.000 description 4
238000002485 combustion reaction Methods 0.000 description 4
238000006731 degradation reaction Methods 0.000 description 4
235000011180 diphosphates Nutrition 0.000 description 4
239000006185 dispersion Substances 0.000 description 4
239000000463 material Substances 0.000 description 4
239000003921 oil Substances 0.000 description 4
229920003023 plastic Polymers 0.000 description 4
239000004033 plastic Substances 0.000 description 4
239000001294 propane Substances 0.000 description 4
229920002803 thermoplastic polyurethane Polymers 0.000 description 4
239000004416 thermosoftening plastic Substances 0.000 description 4
239000002023 wood Substances 0.000 description 4
229920006347 Elastollan Polymers 0.000 description 3
239000004698 Polyethylene Substances 0.000 description 3
229920001587 Wood-plastic composite Polymers 0.000 description 3
150000001336 alkenes Chemical class 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
230000008859 change Effects 0.000 description 3
239000008162 cooking oil Substances 0.000 description 3
238000009826 distribution Methods 0.000 description 3
238000007710 freezing Methods 0.000 description 3
230000008014 freezing Effects 0.000 description 3
239000011521 glass Substances 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
229920000620 organic polymer Polymers 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 3
229920001343 polytetrafluoroethylene Polymers 0.000 description 3
239000004810 polytetrafluoroethylene Substances 0.000 description 3
230000001681 protective effect Effects 0.000 description 3
229940048084 pyrophosphate Drugs 0.000 description 3
229940005657 pyrophosphoric acid Drugs 0.000 description 3
229920005989 resin Polymers 0.000 description 3
239000011347 resin Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000010409 thin film Substances 0.000 description 3
238000001291 vacuum drying Methods 0.000 description 3
239000011155 wood-plastic composite Substances 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
229920003314 Elvaloy® Polymers 0.000 description 2
229920000877 Melamine resin Polymers 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
229920003182 Surlyn® Polymers 0.000 description 2
HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000002411 adverse Effects 0.000 description 2
LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 2
229910000387 ammonium dihydrogen phosphate Inorganic materials 0.000 description 2
229920001276 ammonium polyphosphate Polymers 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
230000006652 catabolic pathway Effects 0.000 description 2
235000019504 cigarettes Nutrition 0.000 description 2
238000004891 communication Methods 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
238000004132 cross linking Methods 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
230000007812 deficiency Effects 0.000 description 2
230000001627 detrimental effect Effects 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
239000005038 ethylene vinyl acetate Substances 0.000 description 2
239000010419 fine particle Substances 0.000 description 2
239000004519 grease Substances 0.000 description 2
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 2
235000019837 monoammonium phosphate Nutrition 0.000 description 2
239000006012 monoammonium phosphate Substances 0.000 description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
150000002894 organic compounds Chemical class 0.000 description 2
235000021317 phosphate Nutrition 0.000 description 2
239000011120 plywood Substances 0.000 description 2
229920001155 polypropylene Polymers 0.000 description 2
239000000843 powder Substances 0.000 description 2
WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
239000000376 reactant Substances 0.000 description 2
230000000717 retained effect Effects 0.000 description 2
238000009987 spinning Methods 0.000 description 2
230000001629 suppression Effects 0.000 description 2
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
239000004711 α-olefin Substances 0.000 description 2
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
XYUINKARGUCCQJ-UHFFFAOYSA-N 3-imino-n-propylpropan-1-amine Chemical compound CCCNCCC=N XYUINKARGUCCQJ-UHFFFAOYSA-N 0.000 description 1
239000004254 Ammonium phosphate Substances 0.000 description 1
239000004114 Ammonium polyphosphate Substances 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
229920003345 Elvax® Polymers 0.000 description 1
229920000784 Nomex Polymers 0.000 description 1
FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
239000012963 UV stabilizer Substances 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
229910000148 ammonium phosphate Inorganic materials 0.000 description 1
235000019289 ammonium phosphates Nutrition 0.000 description 1
235000019826 ammonium polyphosphate Nutrition 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000003466 anti-cipated effect Effects 0.000 description 1
239000010426 asphalt Substances 0.000 description 1
238000003339 best practice Methods 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000004020 conductor Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
230000004069 differentiation Effects 0.000 description 1
IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000010410 dusting Methods 0.000 description 1
238000010292 electrical insulation Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
239000002360 explosive Substances 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
230000006870 function Effects 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
230000020169 heat generation Effects 0.000 description 1
239000012760 heat stabilizer Substances 0.000 description 1
230000002209 hydrophobic effect Effects 0.000 description 1
230000006872 improvement Effects 0.000 description 1
239000012796 inorganic flame retardant Substances 0.000 description 1
229920000592 inorganic polymer Polymers 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
ZQKXQUJXLSSJCH-UHFFFAOYSA-N melamine cyanurate Chemical compound NC1=NC(N)=NC(N)=N1.O=C1NC(=O)NC(=O)N1 ZQKXQUJXLSSJCH-UHFFFAOYSA-N 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
239000000178 monomer Substances 0.000 description 1
150000004712 monophosphates Chemical class 0.000 description 1
230000008450 motivation Effects 0.000 description 1
DTSDBGVDESRKKD-UHFFFAOYSA-N n'-(2-aminoethyl)propane-1,3-diamine Chemical compound NCCCNCCN DTSDBGVDESRKKD-UHFFFAOYSA-N 0.000 description 1
BOUNXJOSVRWQIH-LYBHJNIJSA-N n-[(6e)-3-(2-amino-1,4,5,6-tetrahydropyrimidin-6-yl)-6-[(carbamoylamino)methylidene]-9,12-bis(hydroxymethyl)-2,5,8,11,14-pentaoxo-1,4,7,10,13-pentazacyclohexadec-15-yl]hexadecanamide Chemical compound N1C(=O)\C(=C/NC(N)=O)NC(=O)C(CO)NC(=O)C(CO)NC(=O)C(NC(=O)CCCCCCCCCCCCCCC)CNC(=O)C1C1NC(N)=NCC1 BOUNXJOSVRWQIH-LYBHJNIJSA-N 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
239000004763 nomex Substances 0.000 description 1
238000013021 overheating Methods 0.000 description 1
108700016304 palmitoyl tuberactinamine N Proteins 0.000 description 1
230000036961 partial effect Effects 0.000 description 1
230000037361 pathway Effects 0.000 description 1
239000008188 pellet Substances 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
125000004437 phosphorous atom Chemical group 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
238000005036 potential barrier Methods 0.000 description 1
238000005381 potential energy Methods 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000012545 processing Methods 0.000 description 1
230000002250 progressing effect Effects 0.000 description 1
230000000644 propagated effect Effects 0.000 description 1
AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
239000011253 protective coating Substances 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
230000002787 reinforcement Effects 0.000 description 1
238000012552 review Methods 0.000 description 1
238000009751 slip forming Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229910001415 sodium ion Inorganic materials 0.000 description 1
239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
238000002207 thermal evaporation Methods 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000013585 weight reducing agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K21/00—Fireproofing materials
- C09K21/06—Organic materials
- C09K21/12—Organic materials containing phosphorus
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62C—FIRE-FIGHTING
- A62C3/00—Fire prevention, containment or extinguishing specially adapted for particular objects or places
- A62C3/02—Fire prevention, containment or extinguishing specially adapted for particular objects or places for area conflagrations, e.g. forest fires, subterranean fires
- A62C3/0278—Fire prevention, containment or extinguishing specially adapted for particular objects or places for area conflagrations, e.g. forest fires, subterranean fires by creating zones devoid of flammable material
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C211/09—Diamines
- C07C211/10—Diaminoethanes
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3839—Polyphosphonic acids
- C07F9/3873—Polyphosphonic acids containing nitrogen substituent, e.g. N.....H or N-hydrocarbon group which can be substituted by halogen or nitro(so), N.....O, N.....S, N.....C(=X)- (X =O, S), N.....N, N...C(=X)...N (X =O, S)
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K7/00—Use of ingredients characterised by shape
- C08K7/02—Fibres or whiskers
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K21/00—Fireproofing materials
- C09K21/14—Macromolecular materials
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen

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Chemical & Material Sciences (AREA)
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Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Polymers & Plastics (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Biochemistry (AREA)
Textile Engineering (AREA)
Materials Engineering (AREA)
Biodiversity & Conservation Biology (AREA)
Emergency Management (AREA)
Business, Economics & Management (AREA)
Public Health (AREA)
Forests & Forestry (AREA)
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Compositions Of Macromolecular Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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CA2969239A 2014-12-12 2015-12-12 Method for preparing sodium free ethyleneamine polyphosphate (eappa) for flame retardant uses Active CA2969239C (en)

Applications Claiming Priority (11)

Application Number	Priority Date	Filing Date	Title
US201462091457P	2014-12-12	2014-12-12
US62/091,457		2014-12-12
US201562110560P	2015-02-01	2015-02-01
US62/110,560		2015-02-01
US201562120465P	2015-02-25	2015-02-25
US62/120,465		2015-02-25
US201562202090P	2015-08-06	2015-08-06
US62/202,090		2015-08-06
US201562246037P	2015-10-24	2015-10-24
US62/246,037		2015-10-24
PCT/US2015/065415 WO2016094887A2 (en)	2014-12-12	2015-12-12	Flame retardant and flame retardant uses

Publications (2)

Publication Number	Publication Date
CA2969239A1 CA2969239A1 (en)	2016-06-16
CA2969239C true CA2969239C (en)	2022-04-26

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Country Status (8)

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US (1)	US10501602B2 (de)
JP (1)	JP6736555B2 (de)
CN (1)	CN107001696B (de)
AU (1)	AU2015360243B2 (de)
CA (1)	CA2969239C (de)
DE (1)	DE112015004677B4 (de)
GB (1)	GB2549015B (de)
WO (1)	WO2016094887A2 (de)

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AU2019277078A1 (en) *	2018-05-28	2020-12-17	Robert Valentine Kasowski	FR compositions with additives for drip
CN112292426B (zh) *	2018-06-13	2023-06-23	株式会社Adeka	聚磷酸胺盐组合物、聚磷酸胺盐阻燃剂组合物、含有其的阻燃性合成树脂组合物及其成型体
CA3150494A1 (en) *	2019-09-23	2021-04-01	Robert Valentine Kasowski	PHOSPHORUS-NITROGEN ALTERNATIVE TO PFC FOAM
US11415245B2 (en)	2020-05-20	2022-08-16	Aah Holdco, Llc	Double jacketed, high temperature fire hose
EP4182589A4 (de)	2020-07-16	2024-07-31	All American Holdings Llc	Hochfester mehrzweckschlauch
CN113337007B (zh) *	2021-04-28	2023-03-10	佳化化学（抚顺）新材料有限公司	液体阻燃剂、阻燃硅橡胶及其制备方法和应用
EP4377404A1 (de) *	2021-07-28	2024-06-05	Robert Valentine Kasowski	Fluorfreie tenside und schaumzusammensetzungen
CN115232445B (zh) *	2022-09-19	2022-12-09	纽宝力精化(广州)有限公司	一种阻燃型环氧树脂及其制备方法

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2015
- 2015-12-12 GB GB1708920.2A patent/GB2549015B/en active Active
- 2015-12-12 CN CN201580067692.4A patent/CN107001696B/zh active Active
- 2015-12-12 CA CA2969239A patent/CA2969239C/en active Active
- 2015-12-12 AU AU2015360243A patent/AU2015360243B2/en not_active Ceased
- 2015-12-12 DE DE112015004677.1T patent/DE112015004677B4/de active Active
- 2015-12-12 US US15/323,960 patent/US10501602B2/en active Active
- 2015-12-12 WO PCT/US2015/065415 patent/WO2016094887A2/en active Application Filing
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Also Published As

Publication number	Publication date
GB201708920D0 (en)	2017-07-19
CN107001696B (zh)	2020-01-07
US20170204250A1 (en)	2017-07-20
CN107001696A (zh)	2017-08-01
AU2015360243B2 (en)	2020-01-30
CA2969239A1 (en)	2016-06-16
GB2549015A (en)	2017-10-04
AU2015360243A1 (en)	2017-07-27
JP6736555B2 (ja)	2020-08-05
DE112015004677B4 (de)	2021-04-01
DE112015004677T5 (de)	2017-07-06
JP2018508594A (ja)	2018-03-29
GB2549015B (en)	2022-01-12
WO2016094887A3 (en)	2016-08-11
US10501602B2 (en)	2019-12-10
WO2016094887A2 (en)	2016-06-16

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